10 Of The Most Stylish Harley-Davidson Motorcycles Ever Designed

Harley-Davidson needs no introduction. It is a name synonymous with the open road, the rumble of a powerful engine, and the undeniable aura of freedom. Harley-Davidson has been crafting motorcycles for over a century, each with its own unique personality and style — they are rolling works of art.

We all know that Harley-Davidson is iconic, but some models stand out from the pack. These are the bikes that make heads turn, spark conversations, and get immortalized in movies and TV shows — we are talking about the most stylish Harley-Davidson motorcycles ever designed.

In this article, we'll look at 10 of the most stylish Harley-Davidson motorcycles ever designed. Each bike on this list has its own story and look — showing just how Harley-Davidson blends style and performance. If you are a die-hard Harley enthusiast or simply appreciate the beauty of a well-designed machine, get ready for a ride through some of the best Harley-Davidson motorcycles to ever hit the road.

We start our list with the Harley-Davidson Dyna Wide Glide, a shining star among motorcycles. This bike has captured the hearts of many riders with its laid-back chopper style and classic Harley attitude. The Dyna Wide Glide's design is both timeless and distinctive, making it a favorite among Harley enthusiasts.

The Dyna Wide Glide instantly grabs your attention with its raked-out front end and wide handlebars. It gives it that unmistakable custom chopper vibe straight off the showroom floor. The devil is in the details, and those details are what makes it extraordinary. The blacked-out engine, chrome accents, and minimalist styling give it a tough, no-nonsense look. The flame graphics on the tank add a touch of flair without going overboard.

The Dyna Wide Glide — one of the most successful Harley-Davidson motorcycles in history — is powered by Harley's Twin Cam engine, which delivers plenty of torque and a satisfying rumble. This engine is known for its reliability and performance and gives riders the power they need without sacrificing smoothness. The six-speed transmission allows for easy cruising at highway speeds, making this bike as functional as it is stylish.

Sink into the low-slung seat, stretch out to the forward foot controls, and you are ready to eat up the miles in comfort — no matter whether it is a quick trip across town or a cross-country adventure.

The second on our list is the Harley-Davidson Night Rod Special, a bike that grabs attention everywhere it goes. This motorcycle is all about attitude and style with its sleek, blacked-out design and powerful performance. It is powered by the Revolution engine, a liquid-cooled V-Twin developed with help from Porsche.
The Night Rod Special has an aggressive stance and low profile. The all-black paint job, including the frame and engine, gives it a tough and stealthy look. The drag-style handlebars and forward controls put you in a commanding position. The inverted front forks and dual disc brakes give it a sporty feel, and the low seat and compact frame make it surprisingly nimble for its size. The bike's wide rear tire not only looks impressive but also provides excellent grip and stability.
Riding the Night Rod Special is an experience that combines Harley-Davidson's classic style with a modern, performance-oriented edge. It looks great and rides even better, with a smooth and powerful feel that's bound to impress. For those who want a motorcycle that's both stylish and high-performing, the Night Rod Special is a top pick.

The list of the most stylish Harley-Davidson bikes would be incomplete without the mention of Harley-Davidson Fat Boy. It is one of those bikes everyone recognizes — even if they don't know much about motorcycles. With its muscular design and solid build, the Fat Boy has been a favorite among riders since its debut in 1990. But how Harley-Davidson's famous Fat Boy motorcycle came to be is a story of innovation and bold design choices.

One of the first things you notice about the Fat Boy is its chunky look. The wide front forks, large headlight, and fat tires give it a powerful presence. The solid disc wheels make it instantly recognizable on the road. The low seat and wide handlebars provide a comfortable riding position, perfect for long cruises.

Riding the Fat Boy is an experience in itself. It is powered by Harley's Twin Cam engine, which provides smooth and reliable performance. The bike handles well for its size, giving it a smooth ride typical of Harley's Softail line. The suspension is designed to absorb bumps and provide comfortability, whether on a short trip or a long haul.

One interesting fact about the Fat Boy is its appearance in the movie "Terminator 2: Judgment Day". Arnold Schwarzenegger's character famously rides a Fat Boy, cementing its status as a pop culture icon. This appearance helped boost the bike's popularity and showcased its tough, rugged appeal.

The Harley-Davidson XR-750 is a legend in the world of flat-track racing. Known for its speed and agility, this bike has dominated tracks and won countless championships since its debut in 1970. It is not just a race bike, though. The XR-750's design and performance have made it an icon among motorcycle enthusiasts and one of the rarest Harley-Davidson motorcycles ever built.

One cannot overlook its striking minimalist aesthetic. The bike has a stripped-down look that highlights its functionality. The slim fuel tank, narrow frame, and lightweight construction all contribute to its agility on the track. The XR-750 was created to replace the aging KR series and quickly proved itself. The XR-750's performance on the track has earned it a reputation as one of the best racing motorcycles ever made.

The XR-750 is also known for its influence on motorcycle culture and design. The famous stunt performer Evel Knievel used a modified XR-750 for many of his record-breaking jumps. This cemented the bike's status as an icon of daring and adventure.

The Harley-Davidson V-Rod is a bike that broke the mold when it was introduced. With its hi-tech design, stunning styling, and powerful performance, it represented a bold step for Harley-Davidson into the world of muscle bikes. Its sleek, modern look included a hydroformed frame, forward-mounted foot controls, and a streamlined profile. This bold design choice aimed to attract a new generation of riders.
One of the first things you notice about the V-Rod is the unique fuel tank location, which is actually under the seat. This design choice allowed for a lower center of gravity, improving the bike's handling and giving it a distinctive look. The long, low frame and wide rear tire give the V-Rod a beefy stance that commands attention.
The V-Rod was the first Harley-Davidson to feature liquid cooling. Similar to the Night Rod Special, the V-Rod also features a Revolution engine, developed in partnership with Porsche. This liquid-cooled, DOHC V-twin engine is more than just about raw power — it is also incredibly smooth and reliable. The sleek aluminum bodywork, polished aluminum frame, and distinctive radiator shroud give it a futuristic look. The bike's instrumentation is minimalist but functional and keeps the focus on the ride.

The Harley-Davidson Night Train is all about that dark and edgy vibe. Launched in 1998, it quickly became a hit with riders who love the minimalist and blacked-out look. Everything about the Night Train screams attitude, and you can see it in every detail.
The bike's black-on-black color scheme is one of the first things that grab your attention. From the frame to the engine and exhaust, nearly every part of the Night Train is bathed in black. The minimalist design extends to the drag-style handlebars and simple, clean lines of the bike.
Underneath its dark exterior, the Night Train is powered by Harley's Twin Cam 88B engine. The B in 88B stands for "balanced," as this engine has a counterbalancer to reduce vibration, which means a smoother ride. The forward foot controls and low seat height give riders a stretched-out and comfortable riding position. The bike's long front forks and narrow front wheel enhance its appearance while maintaining good handling and stability.
One interesting fact about the Night Train is its connection to custom bike culture. Due to its stripped-down, bare-bones design, the Night Train has become a popular choice for custom builders. Its simple and blacked-out canvas offers endless possibilities for personalization and customization.

The Harley-Davidson CVO Softail Convertible is a bike that combines luxury with versatility. As a part of Harley's Custom Vehicle Operations (CVO) lineup, this motorcycle is designed for those who want the best of both worlds — a stylish cruiser that can easily transform into a touring bike.
The bike's design is a blend of classic Harley-Davidson styling and modern touches. The custom paint job, chrome accents, and unique badging give it a look that stands out in any crowd. The leather saddlebags and seat add a touch of luxury and the fairing provides wind protection for long rides. One of the many features of the CVO Softail Convertible is its quick-detach elements — the windshield, saddlebags, and passenger pillion can all be removed in minutes. You can switch from a touring setup to a sleek cruiser look in no time.
An interesting fact about the CVO Softail Convertible is its limited production, making it a model sought after among collectors and enthusiasts. The attention to detail and high-quality materials used in its construction reflects Harley-Davidson's commitment to creating top-tier motorcycles.

Next up on the list is a bike that blends comfort, style, and performance seamlessly — the Harley-Davidson Street Glide Special. One of the first things that you notice about the Street Glide Special is its sleek and streamlined design. The batwing fairing is a signature element and provides excellent wind protection while adding to the bike's aggressive look. The stretched saddlebags and low-profile seat enhance its sleek silhouette — it looks just as good parked as it does on the road.

The bike's infotainment system is another highlight. The Boom! Box system features a touchscreen display, navigation, and Bluetooth connectivity all adding to its stylish appearance. The high-quality audio system provides clear sound — even at high speeds — making those long rides more enjoyable.

One interesting fact about the Street Glide Special is its popularity among custom builders. It is a perfect canvas for customization due to its stylish yet functional design. Many riders personalize their Street Glide with unique paint jobs, custom seats, and performance upgrades, making each bike unique. Make sure to check out All About The 2019 Harley-Davidson Street Glide Motorcycle to read about additional details and insights.

The Harley-Davidson Softail Slim is a bike that beautifully combines vintage style with modern performance. It is a nod to the bobber motorcycles of the past with its minimalistic design and stripped down look. If you are into classic aesthetics with a contemporary twist, the Softail Slim is a bike worth admiring.

The Softail Slim has a low-slung profile—perfect for instilling confidence in shorter riders who are just starting out. The solo seat, narrow rear end, and Hollywood handlebars give it an old-school vibe reminiscent of the 1940s and 1950s motorcycles. This bike looks like it rolled straight out of a classic movie, yet it is equipped with modern technology that ups its performance and reliability. The bike's lightweight frame and low center of gravity make it one of the most popular Harley-Davidson cruisers for beginner riders.

While the Softail Slim looks vintage, it includes features like keyless ignition, LED lighting, and advanced suspension. The hidden rear shocks preserve the classic hardtail look without sacrificing comfort and provide a smooth ride over various terrains. Riding the Softail Slim feels like stepping back in time but with all the benefits of modern engineering. The minimalist design means there's nothing unnecessary on this bike — just pure riding pleasure.

The Harley-Davidson Fat Bob 114 is a bold and aggressive bike that turns heads wherever it goes. This bike stands out in the Harley-Davidson lineup with its rugged style and powerful performance — especially if you want something a bit more rebellious.
The Fat Bob 114 features a distinctive rectangular LED headlight and a chunky muscular frame. The inverted front forks and dual disc brakes enhance its aggressive stance and improve its handling and stopping power. The fat tires — both front and rear — give the bike a solid grip on the road and add to its tough appearance. The bike's lightweight Softail frame and optimized suspension make for a smooth and responsive ride even on rough roads.
Riding the Fat Bob 114 is an experience in itself. The bike's seating position is comfortable, with a slightly forward lean that adds to its aggressive feel. The digital instrumentation is sleek and modern and provides all the necessary information without cluttering the handlebars. The dual exhaust pipes not only look great but also produce a deep and satisfying roar that Harley fans love.